Below are three lessons that I find especially pertinent to
running a successful Silicon Valley business.

From Larry Ellison, Oracle founder/CEO:

“Sometimes, you need to piss off the boss.”

Leading up to the meeting, we really needed to brief Larry on
what MCI was looking to hear. However, Larry was eternally
busy; everyone wanted his time. He didn’t reply to emails or
voicemails; stalking his office was fruitless; but
we needed him at this meeting. First,
I’ll tell you the story of how I trapped Larry Ellison in his car
in a secluded parking lot one night. This was around 1994. I was
on Oracle’s sales team and handled the MCI account. A sales
colleague and I were bringing MCI’s CTO and top 8 CIO’s to
Oracle’s headquarters, to hear about Oracle’s vision for the
Internet. It was early days of the Internet, when Netscape
had not yet gone public; MCI owned half of the Internet backbone
in the US, and Vint Cerf, “father of the Internet”, was working
at the company.

At the end of the day, as we were leaving Oracle, we spotted
Larry getting into his red Acura NSX, a phalanx of PR people
holding out press releases for him to review. This was our
chance! We pulled up in front of Larry, blocking his exit.
Larry’s eyes bulged when he saw the doors swinging open on
a black Lincoln town car, with two guys in dark suits
simultaneously exiting from either side. When he realized
it was his sales team, and not a hit squad, he snatched the 2
page briefing doc from our hands, slammed on the gas and roared
off.

In the end, we did get what we needed. Larry waxed
eloquently on Oracle’s strategy for the Internet (a strategy that
Marc Benioff put together, by the way), and it was a hit.
My car, for the record, never even got dented. So it was a
net win for us.

In 2003, fresh in my role as the first CMO at Salesforce.com, I
got a call from Marc for what would be the first in a series of
outlandish marketing campaigns, each one more creative than the
last. In the SaaS world, our new releases would trickle out
on a regular cadence, without much fanfare. Marc wanted to
change that, and turn our releases into a platform for big
product announcements. He told me to name our release “S3”,
to buy all the tickets to the San Francisco movie premier of
Terminator 3, and how we were going to do a “S3 at T3” launch
with 500 people in attendance. Oh, and he wanted me to
raise $250K through partner sponsorships.

I had serious doubts about this, and I could think of 100
reasons why not to do it including the fact that we were an
enterprise software company, not Hollywood hotshots. No one had
done anything like this before. But I suspended my
disbelief, pulled the team together, and lo and behold, we
executed a world class event that was attended by and written
about by local and national press. And I have my photo
shaking hands with Arnold!

What I learned from Marc is that most of us
walk around with an artificial glass ceiling on what we can
accomplish. We find 100 reasons why an idea won’t work.
This holds us back from reaching our true potential.
What I learned from Marc is to constantly smash that glass
ceiling, to take chances and push yourself beyond your comfort
level, and tap into a whole new world of possibilities. At the
end of the day, you want to be writing the rule book rather than
abiding by one.

From Scott Thompson, Yahoo
CEO:

“Your job is to make people successful”

Towards the end of 2009, I was almost two years into co-founding
Zuora. Things were going well for us. In a tough
economic year, we were on target to triple the company’s size, in
terms of revenue, cash, and number of customers. At my
quarterly one-on-one lunch with our board member Scott Thompson,
who was President of eBay’s PayPal business at the time, I was feeling
pretty good about myself. Scott could see that I was feeling like
we had “made it.”

Immediately, Scott took me down a peg, saying, “This
progress is great, but if you asked me for advice, and you
haven’t asked me by the way, I would say the one thing you
haven’t proved is that you can make your people successful.”

That came as a bit of a shock to me. It took me awhile to
internalize, but I understood what Scott was saying. He has
observed that my style was to throw projects at people, and then
let them sink or swim. If they sunk, I’d simply give the
project to someone else. Zuora was successful, but it came
at the expense of being a rough place to work! If I wanted
to help Zuora scale to greatness, my focus needed to shift from
just focusing on the company’s success, to the employee’s
success.

“You are the CEO,” Scott said. “That’s your job. you’re on the
hook and you have to own that
responsibility.”

Scott, thanks for the wake up call, it was
very timely. At the end of 2009, I saw the need to
dramatically shift our strategy to pursue a much greater market
opportunity – the Subscription Economy. But to pursue this
strategy, we needed everyone in the company to take on greater
roles. I realized that my job was to lay out our vision and
priorities, and get out of their way. So I took the company
to a two-day off-site where we talked about our core values.
We talked about how we weren’t at Zuora for just a job, of
how everyone wanted to be empowered to be their very best.
We invented the word “ZEO”: the idea that everyone at Zuora
is in charge of their own destiny and can be their own CEO.
The ZEO philosophy has been key to our company’s
success.

The reality is that everybody’s experiences
are different in the Valley. Ask Aaron Levie or Aneel Bhusri. They all have different stories
about moments of clarity and lessons learned, often painfully.
But any of them will tell you that the good, the bad and the ugly
has made them what they are today.